Known for its lush, rolling hills, world-famous wine and luxurious hotels, Tuscany is a bucket-list destination. The Italian region is heavy on indulgence—vacations here are defined by Brunello-filled days, truffle-rich fare, visits to romantic hilltop towns and overnights at plush countryside resorts—but, traditionally, it has not been seen as a winter destination. However, the Indagare-adored Rosewood Castiglion del Bosco—one of the most iconic hideaways in the idyllic Tuscan hills—is aiming to make winter in Tuscany as enjoyable as it is at other times of the year. The resort is keeping all 11 of its pampering villas open year-round, and nearly every activity and attraction that lures travelers to Tuscany in the warmer months is still available, so guests can enjoy the world-famous region both without the summer crowds and at a significantly reduced price.
After testing out the winter villa program by opening a handful of villas for the 2016-2017 season, Castiglion del Bosco received such high interest that they expanded the program the following year. From November to late March, the resort’s 11 two- to six-bedroom estates act as true rental properties—the main hotel and its facilities are closed—but come with full staffs and ample amenities, including access to the hotel’s 18-hole private golf course and its Brunello di Montalcino winery, as well as the option to arrange in-villa yoga, cooking classes and spa treatments. Occupying restored 17th- and 18th-century farmhouse, the CdB villas were immaculately styled by Chiara Ferragamo, who owns the 5,000-acre estate with her husband, Massimo. Decked out with fireplaces and full kitchens, the homes are ideal for winter escapes, and some even feature pizza ovens, home theaters and tennis courts.
The wintertime activities in Tuscany are nearly as robust as they are during the summer months. On-property pursuits include horseback riding, biking and hiking, and the villa staff can also arrange Ferrari tours, hot air ballooning and helicopter rides. The resort is ideally situated for day trips into the southern Tuscan region, whether to storied towns like Siena or Montalcino or to a truffle farm to hunt for the lauded savory treasure. The holiday season welcomes a number of lovely Christmas markets, which are fun to visit for stocking stuffers. Also popular during the chilly months are the Roman-era hot springs located just a short drive away. With ample activities, plush lodgings and incredible cuisine, winter in Tuscany is just as enjoyable as it is in the summer, but much more peaceful.
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